Karl schranz



Patented July 31, 1928.

, UNITED STATES PATENT OFFICE.

KARL SCHRANZ, OF ELBERFELD, AND CLEMENS LUT'IER, OF BARMEN-LANGENFELD', GERMANY, ASSIGNORS TO WINTHROP CHEMICAL COMPANY, INC., 01 NEW YORK,

1-ALKOXYMETHYL-3.7-DIMETHYLXANTHINES.

No Drawing. Application filed February 19, 1926. Serial No. 89,413, and in Germany May 23, 1925.

In our earlier application Ser. No. 41,870 (now Patent No. 1,616,282) filed July 6, 1925, the hitherto unknown 1-1netl1oXymethyl-3.7- dimethylxanthine is described Which acts 5 like caft'ein on the'human body.

We have now found that also the higher homologues having most probably the for- R standing for an alkyl other than methyl, possess diuretic properties. They form double salts with organic acid salts. To-

gether with a salicylate solution they furnish neutral solutions for subcutaneous use.

In order to illustrate the new process more fully the following example is given, the 0 parts being by weight A mixture of 200 parts by weight of theobromine (sodium salt), 200 parts by weight of benzene and 105 parts by weight of chlorinethylethylether ClCH OCl H is heated in an autoclave during 5 hours to 120 C. The 1-ethoXyinethyl-3.7-dimethyl- Xanthine is isolated by extraction with benzene and crystallized from water. It crystallizes in needles melting at 152-153 C.

Other caifein ethers may be produced in this way from theobromine salts e. g.

1 isopropyloxymethyl 3.7 dimethylxanthine melting point 107-108 C.

l-n-propyloxymethyl 3.7 dimethylxanthine melting point 130132 C.

1-n-butyloxymethyl-3.7 dimethylxanthine melting point 102103 C.

1-isobutyloxymethyl-3.7-dimethylxanthine melting point 128-129" C.

1 benzyloxymethyl 3.7 -dimethylxanthine melting point 9597 C.

1 allyloxymet hyl 3.7 dimethyl'xanthine melting point 108110 C.

We claim: 1. The process of producing l-alkoxymethyl-B.7-dimethylxanthines, which process consists in treating a theobromine salt with chloroalkylether formula ClCH alkyl group cont having most probably the OR R standing for an aining two or more carbon atoms. substantially as described.

2. The process of producing l-ethoxymethscribed.

3. The herein described l-alkoxymethyl- 3.7-dimethylxanthines having most probably the formula in which R deno tes an alkyl group containing two or more carbon atoms, being crystalline products formingdouble salts W1th salts of organic acids and possessing diuretic properties, subst antially as described.

4. The herein described l-ethoxymethyl- 3.7-dimethylxanthine water in the sh crystallizing from ape of needles melting at- 152153 C. forming double salts With salts of organic acid s and possessing diuretic properties, substantially as described.

In testimony whereof we have hereunto set our hands.

KARL SGHRANZ. CLEMENS LUTTER. 

